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Molecules 2012, 17(10), 11554-11569; doi:10.3390/molecules171011554

Design and Synthesis of an 18F-Labeled Version of Phenylethyl Orvinol ([18F]FE-PEO) for PET-Imaging of Opioid Receptors

1 ABX Advanced Biochemical Compounds Biomedizinische Forschungsreagenzien GmbH, Heinrich-Glaeser-Strasse 10-14, D-01454 Radeberg, Germany 2 Oslo PET-Centre, Norsk Medisinsk Syklotronsenter AS, N-0027 Oslo, Norway 3 Institute of Basic Medical Sciences, Group of Pharmaceutical Radiochemistry, University of Oslo, Postboks 1110 Blindern, N-0317 Oslo, Norway
* Author to whom correspondence should be addressed.
Received: 13 July 2012 / Revised: 10 September 2012 / Accepted: 11 September 2012 / Published: 28 September 2012
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The semisynthetic oripavine derivative phenethyl orvinol (PEO), a full agonist at opioid receptors (OR), is an attractive structural motif for developing 18F-labeled PET tracers with a high degree of sensitivity for competition between endogenous and exogenous OR-ligands. The target cold reference compound 6-O-(2-fluoroethyl)-6-O-desmethylphenylethyl orvinol (FE-PEO) was obtained via two separate reaction routes. A three-step synthesis was developed for the preparation of a tosyloxyethyl precursor (TE-TDPEO), the key precursor for a direct, nucleophilic radiofluorination to yield [18F]FE-PEO. The developed radiosynthesis provides the target compound in relevantly high yield and purity, and is adaptable to routine production.
Keywords: opioid receptors; PET; agonist; 18F-fluorination; automated radiosynthesis opioid receptors; PET; agonist; 18F-fluorination; automated radiosynthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Marton, J.; Henriksen, G. Design and Synthesis of an 18F-Labeled Version of Phenylethyl Orvinol ([18F]FE-PEO) for PET-Imaging of Opioid Receptors. Molecules 2012, 17, 11554-11569.

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